Chicago

Windy, charming perfection in the Midwest.
— Cynthia P.
  • more about your oliver guide: Cynthia Pillsbury

  • Trip Type: Family /  Summer

  • Ideal Trip Length: 3 days with kids

to & from

From any major city fly into Midway or O’Hare. No need to have a car; uber or walk everywhere!

Stay

  • Chicago Athletic Association (CAA): built in 1893 and recently restored, is a perfect place to call home whether you are with your kids, friends, husband or alone! The location is across from Millennium Park which is central and provides a great view.
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Eat & Drink

  • Cindy’s on the CAA Rooftop: Great food with amazing views, great for lunch, dinner and/or a nightcap on the expansive terrace.
  • Shake Shack: Perfect spot for lunch with kids before you hit the town, can’t find a better burger and fries and shake, imported from New York and it fits right in!

Do

  • Museum Mile: skip the Planetarium, (unless you have a budding astronomer) and spend time at the She'd Aquarium; make sure to buy tickets to a sea animal experience. The Field Museum (Natural History) is also worthwhile.
  • Millennium Park: Climb the wall, putt putt golf, stroll through the herb and flower gardens, take in star-lit concert or movie and rent bikes in the park and bike along Lake Michigan.
  • The Art Institute: It’s a big, overwhelming museum so with kids we focused on the traveling exhibit and headed to the basement to see the “miniature rooms” which captured my kids’ attention and mine; incredible to see dollhouse scale home decor from the past 200+ years.
  • Architecture Tour by Boat: These tours by boat are relaxing, fun and interesting and you can get a glass of wine while your kids are engaged in an entertaining oral history lesson of the city’s incredible architecture.

the inside scoop

  • Water Taxi’s are a really fun way to visit Museum Mile to the Navy Pier. You can buy tickets before you board.
  • If you go to the Sky Deck in the Willis Tower make sure you pony up and buy the FAST TRACK pass- it is not worth the time standing in the never ending maze. With the Fast Track you can zip up and experience the Sky Deck but not spend all day getting to it! Not sure it’s worth it if you have anyone with a fear of heights… or crowds.